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Planta Med 2021; 87(08): 600-610
DOI: 10.1055/a-1392-1038
Natural Product Chemistry and Analytical Studies
Original Papers

New Pyrrolobenzoxazine Sesquiterpenoid Derivatives from the Fungus Talaromyces trachyspermus

Boonyanoot Chaiyosang
1   Natural Products Research Unit, Department of Chemistry and Center for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen, Thailand
,
Kwanjai Kanokmedhakul
1   Natural Products Research Unit, Department of Chemistry and Center for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen, Thailand
,
Kasem Soytong
2   Department of Plant Production Technology, Faculty of Agricultural Technology, King Mongkutʼs Institute of Technology Ladkrabang, Bangkok, Thailand
,
Supattra Poeaim
3   Department of Biology, Faculty of Science, King Mongkutʼs Institute of Technology Ladkrabang, Bangkok, Thailand
,
Mayamor Soytong
3   Department of Biology, Faculty of Science, King Mongkutʼs Institute of Technology Ladkrabang, Bangkok, Thailand
,
Sarinya Hadsadee
4   Center for Organic Electronic and Alternative Energy, Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Ubon Ratchathani University, Ubon Ratchathani, Thailand
,
Siriporn Jungsuttiwong
4   Center for Organic Electronic and Alternative Energy, Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Ubon Ratchathani University, Ubon Ratchathani, Thailand
,
Jantana Yahuafai
5   Natural Products Research Section, Research Division, National Cancer Institute, Bangkok, Thailand
,
Pongpun Siripong
5   Natural Products Research Section, Research Division, National Cancer Institute, Bangkok, Thailand
,
Somdej Kanokmedhakul
1   Natural Products Research Unit, Department of Chemistry and Center for Innovation in Chemistry, Faculty of Science, Khon Kaen University, Khon Kaen, Thailand
› Author AffiliationsSupported by: Thailand Research Fund DBG6180029
Supported by: Thailand Research Fund_Royal Golden Jubilee Ph.D. program and Khon Kaen University PHD/0105/2560
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Abstract

Three new pyrrolobenzoxazine sesquiterpenoids, talatrachyoxazines A – C (1 – 3), together with fourteen known compounds (4 – 17), were isolated from the fungus Talaromyces trachyspermus EU23. Their structures were identified by spectroscopic evidence and mass spectrometry. The absolute configurations of 1 – 3 were determined by NOESY data and comparison of their calculated and experimental electronic circular dichroism (ECD) spectra. Compound 1 showed cytotoxic activity against HelaS3, KB, HT-29, MCF-7, and HepG2 cell lines with IC50 values of 7, 11, 10, 12, and 10 µM, respectively. Compounds 1 and 14 showed weak antibacterial activity against the gram-positive bacteria Bacillus cereus and Bacillus subtilis, while 1 – 3 and 14 showed weak antibacterial activity against the gram-negative bacterium Pseudomonas aeruginosa. In addition, compound 1 showed weak antibacterial activity against Escherichia coli.

Key words

Trichocomaceae - Talaromyces - Talaromyces trachyspermus - pyrrolobenzoxazine - talatrachyoxazine - cytotoxicity

Supporting Information

    HR-ESI-TOF-MS and 1D and 2D NMR spectra of compounds 1 – 3, spectroscopic data of 4 and 5, dose-response curves for cytotoxic activity, and full antimicrobial data are available as Supporting Information.

  • Supporting Information


Publication History

Received: 27 April 2020

Accepted after revision: 06 February 2021

Article published online:
05 March 2021

© 2021. Thieme. All rights reserved.

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